First Mother-Son Pilot Pairing Achieves Milestone for Alaska Airlines

Captain Michelle Miles and first officer Jeff Miles share the flight deck, continuing a three-generation aviation legacy.

Airline pilots Jeff and Michelle Miles [Courtesy: Alaska Airlines]

In a historic moment for Alaska Airlines just ahead of Mother’s Day, captain Michelle Miles and her son, first officer Jeff Miles, recently shared the flight deck, marking the airline’s first mother-son pilot team.

The duo operated a Boeing 737 flight last week from Seattle to Kahului, a city on the Hawaiian island of Maui, fulfilling a lifelong dream for Jeff and continuing a family legacy spanning three generations.

“I’ve waited 27 years for this moment,” Jeff Miles said as he prepared to sit beside his mother in the cockpit.

Not a Coincidence

The pairing was not coincidental. It involved coordinated efforts from Alaska Airlines’ chief pilot’s office to align their schedules, the carrier said, ensuring this milestone could be achieved before Michelle Miles’ planned retirement this fall after 37 years of service.

Michelle’s aviation journey was inspired by her father, captain Richard “Ski” Olsonoski, a retired Navy pilot who joined Alaska in 1981. Reflecting on her career, Michelle recalled the moment.

“Serving as a copilot for my dad was one of the highlights of my career,” she said. “And now, to repeat the experience with my son — well, that’s about as good as it gets.”

Article on father-daughter flight with Alaska [Courtesy: Alaska Airlines]

Jeff’s passion for flying was evident from a young age. He often donned his grandfather’s old Navy flight helmet and imagined himself soaring through the skies.

Michelle, who began flying at 16 and earned her private pilot certificate at 17, served in the U.S. Air Force before joining Alaska in 1988 as its 17th female pilot and the first with a military background.

After attending Big Bend Community College in Washington state, Jeff started his airline flying career at SkyWest. He later joined Alaska in July 2023. Along with Jeff, Michelle’s older son and daughter-in-law are also pilots for other airlines.


Editor’s note: This article first appeared on AirlineGeeks.

Ryan Ewing

Ryan is Sr. Director of Digital for Firecrown's Aviation Group. In 2013, he founded AirlineGeeks.com, a leading trade publication covering the airline industry. Since then, his work has been featured in several publications and news outlets, including CNN, WJLA, CNET, and Business Insider. During his time in the airline industry, he's worked in roles pertaining to airport/airline operations while holding a B.S. in Air Transportation Management from Arizona State University along with an MBA. Previously, he worked for a Part 135 operator and later a major airline. Ryan is also an Adjunct Instructor at Embry-Riddle Aeronautical University.
Sign-up for newsletters & special offers!

Get the latest stories & special offers delivered directly to your inbox.

SUBSCRIBE